


These Twisting Roads

by hiddenheadspace (orphan_account)



Category: Supernatural
Genre: Bisexual Character, Character Study, Crossdressing, Drag Queens, Gay Pride Parade, Homophobia, John Winchester's Bad Parenting, M/M, Masturbation, Pink Panties, Sexual Experimentation, Sexuality, romance is not the focus, sam is unintentionally a good brother yay sam, the relationship tags are really just there because they're referenced
Language: English
Status: Completed
Published: 2013-10-20
Updated: 2013-10-20
Packaged: 2017-12-29 22:38:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,665
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1010950
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/hiddenheadspace
Summary: <blockquote class="userstuff">
              <p>Four times in Dean Winchester's life where he was Not As Straight as he Should Have Been.</p>
            </blockquote>





	These Twisting Roads

The first time he could remember was in the summer of 1988. Dad was driving with him and Sam slumped in the backseat. The outside wasn’t unbearable, but it was enough to make everything sticky and tiring.

Dad made a quiet noise from the front. “Don’t look, Sam,” he said.

Sam, of course, hadn’t even been paying attention. His concentration was then pulled out of his puzzle book to the outside. Dean hastily, guiltily, yanked his gaze away from the signs and colors and people. There was noise from the parade, too, people shouting and maybe singing, filtering into the car despite the way John clearly wished it wouldn’t.

“What are they doing?” Sam asked innocently while Dean slumped lower and drummed his feet on the ground.

“Never you mind,” Dad said shortly. Sam pouted and stared out the windows avidly, at least until Dad found an alternate route that took them all away from the marching people.

* * *

 

The second time was years later. 

Yeah, Sam had always been a rebellious kid, so Dean really shouldn't have felt any surprise at all when Sam decided that the thing to be doing was to go exactly where Dad would deeply disapprove.

This time, it was the gay pride parade.

“Come on, Dean, I don’t want to go alone,” Sam wheedled. Many times. Dean considered refusing just to make Sam not go, but Sam would probably go anyway, and that seemed like a bad plan all around.

So eventually (after Sam had prodded him about it for the better part of an afternoon) he groaned and said, “Fine! I’ll go with you! Happy now?”

Sam was, in fact, happy, which made things a little better.

In any case, Dean ended up standing on a sidewalk next to his wide-eyed brother (and Dean was starting to get the bad feeling that they were being mistaken for a couple by a lot of people) for a long, uncomfortable morning. He wasn’t going to be an asshole to any of these people (bizarre clothing notwithstanding—why did all these men think it necessary to wander around in women’s underwear or stockings?), but he honestly didn’t understand gay people. Girls were great. They were fun and sexy. He just didn’t. Get it. And was now stuck watching a parade with his brother that people were _most fucking definitely_ mistaking for his boyfriend, judging by the winks getting thrown their way.

That was the last straw. “Come on Sam, you’ve had your fun. We’re going back now.”

“Aw, come on!” Sam didn’t look happy about this turn of events. “I _know_ you’re not a homophobic asshole like Dad—”

“ _Sam_ ,” Dean said. “Don’t talk about Dad like that.”

“He is, though,” Sam said mulishly.

“We’re going,” Dean said flatly. Even if he had to drag Sam, he was getting out of there. He bit down on the nagging, uncomfortable feeling in the back of his head that made him talk a little too loudly and quickly.

Sam glowered and dragged his feet and griped, but Dean managed to get him to head back to the motel without too much effort. “Why do you want to leave?” Sam asked petulantly a few times. “ _I_ was having fun.” Dean didn’t really have a good answer to that, so he said nothing.

* * *

 

At that point, there were three things that Dean was certain of, and how he’d ended up in a gay bar wasn’t one of them.   

1\. He probably shouldn’t have been drinking, considering everything.

2\. He was being accosted by a fucking gorgeous drag queen.

3\. _Pink_. _Everywhere._

“So, pretty boy,” Rhonda slurred with a smile that had most definitely broken hearts. “You as hetero as you’re acting?”

He later decided to blame alcohol for how easy it was to shrug and lean closer and say conspiratorially, “Well, I always thought that a little persuasion might do surprising things, but if anyone asks, yep, straight as a fuckin’ arrow.”

“Oh, I bet,” she said, smoothing down her pink dress in a practiced motion. “How’s this, then, Mr. Arrow—you come follow me and we’ll see if your ever so heterosexual self can handle having a little color added to him.”

Dean knew he shouldn’t follow her. But he did.

“This is the men’s room,” he pointed out unnecessarily.

“And I’ve got a dick, don't I? Which, by the way, is taking an interest in that pretty ass of yours.” She full on leered at him before her expression melted back into a friendly smile. “Oops, that was a bit forward of me. One second.” She disappeared into a stall, leaving Dean standing awkwardly outside, wondering what the hell he was getting himself into.

“Alrighty then,” Rhonda said, returning, brandishing a pair of pink panties the exact same shade as her dress. “Put these on.”

Dean could have stopped then, could’ve backed out. Instead he ducked into the stall, fought with his shoes, and put his own underwear in his pocket for lack of a better place to store them. He unlocked the door to find that Rhonda had vanished off to somewhere else, and stood nervously in front of the door for a few moments, trying to pretend that he couldn’t feel the satin rubbing against him with every twitch.

He pushed open the door and made his way back to the bar. Rhonda reappeared and looped an arm around his waist as smooth as anything. “Dean!” She lowered her voice. “So, how you feeling?”

“Bit itchy,” he said casually. “Too much lace.”

She laughed. “You just wait, big boy. We’ll have you in braids by the end of the night if the other girls get any say in this.”

And thus Dean found himself chatting away with more people at the bar, slipping into the atmosphere of the place much more easily than he would have expected.

That was the third time.

* * *

 

The fourth thing was a little more difficult to define, because Dean had been thinking about it for a while. 

Okay, yeah, fine. He liked guys. He was over that. Mostly.

Except…he hadn’t really considered the logistics of what that meant. He had a general idea (and a better sense of what to do, thank you, Rhonda) of what sex entailed (how different could it really be?), but at the same time…Really. Taking it up the ass? He just couldn’t understand how that could be fun.

But, well, he’d had his introduction to All Things Gay, and he figured he should probably initiate himself into the art of gay sex. Maybe he wouldn’t like it after all, and that would be the end of that. (He ignored the idea of liking it, because, weird.)

So, he thought about it, casually. It dwelled on the edges of his mind. No big deal.

Of course, being mid-jacking off always seemed to lower his inhibitions of where he was willing to go. He’d been thinking of guys while getting off for a while, so that was nothing new. The imaginary guy in question had him crowded back against the wall of the shower. Dean shut his eyes tightly as he stroked his dick. The invented dude was muttering dirty things as his hand slid down Dean’s side and to his ass.

That’s when things got interesting. Dean’s imagination decided to run away with itself and next thing Dean knew his fingers had crept down to rub against his hole.

He hadn’t expected the jolt of arousal. His breathing picked up and he pressed a little harder. _Jesus_. The hand he still had on his cock tightened and sped up. His finger pushed in a little, and _fuck_ , no wonder Rhonda had emphasized lube so much if asses were this tight. Lube. He imagined the easy slide it would create, dirty and messy and blinding.

This was nothing like pussy. This was a thousand times tighter and hotter and fuckfuckfuck really easy to stimulate. He pulled back out a little to press on the sensitive rim, sending shocks of urgent need through his body. He came hard and fast and caught himself off-guard. His hand slipped away from his ass and he became aware of how hard he was panting.

“Jesus fuck,” he said aloud, a phrase that he thought summed up that particular experience quite nicely. He could still feel a ghost of the pressure against his hole and a lingering shudder of arousal that curled low and hot at the base of his spine.

“Fuck,” he said once more, because, well. Fuck indeed.

* * *

 

Honestly, while on hunts with Dad or Sam or both, there wasn’t time for much sex with an unexpected gender, and Dean didn’t always find himself attracted to men all that often. Except when he was, and attraction always seemed to hit him like a ton of bricks when it did happen. 

There were a few guys over the years. Not many, certainly nowhere near as many as there were women. A man with gentle, scarred hands while he was on a case in the Deep South caught part of his heart for a little while. Another one, sharp and almost too bright, just about flung him into the dirt from disgust when Dean mistakenly believed he was interested. And, more recently, a fallen angel that Dean could never have anticipated who didn’t back down and thought that there was worth in him that Dean had long stopped believing existed.

Dean was okay with it all, mostly. Maybe he’d taken a long time to really bring himself around to where he was now, but that was alright. All of the pieces of his sexuality had found a way to click together in a way that was close enough to fitting that he didn’t cut himself on the edges of it anymore, and it was nice, he thought as he silently treasured the steadiness of a now-familiar gaze that never fully left him, to have some peace at last. 

**Author's Note:**

> This story draws directly from my own struggles with my sexuality. It was...a little hard to write at times. Please be kind to both Dean and me if you want to leave a comment. 
> 
> Also, Dean uses a few terms that I don't use because they aren't considered accurate anymore—saying "gay pride", for example, while still common, excludes non-gay queer people. Reasoning: a) it's Dean and b) time period.


End file.
